Reaktion #1869169

Reaktionsgleichung

(2S)-2-[{(RS)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-2-hydroxyethyl} amino]propan-1-ol

DCM

sodium triacetoxyborohydride

DCM

DCM

→

(2S)-2-[{(RS)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-2-hydroxyethyl}propylamino]propan-1-ol

Ausbeute 100.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONbefore adding it
2. 2
   Temperaturmaintaining the temperature below 30° C
3. 3
   workup.STIRRINGThe reaction mixture was stirred at 20° C. for 1 hour
4. 4
   Sonstigebefore quenching with an aqueous solution of potassium carbonate (36.4 Kg in 136 L of water)
5. 5
   Sonstigeto separate
6. 6
   WaschenThe organic phase was washed with water (2×23 L)
7. 7
   workup.DISTILLATIONThe equipment was set for distillation and DCM (190 L)
8. 8
   Sonstigewas removed by distillation
9. 9
   Sonstigeto give a final volume of 45 litres
10. 10
    TemperaturThe mixture was cooled to 20° C

Vorschrift

Propioanaldehyde (5.02 Kg, 86.4 mol) was added over 10 minutes to a solution of (2S)-2-[{(RS)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-2-hydroxyethyl} amino]propan-1-ol (22.7 Kg, 78.6 mol) in DCM (123 L) at 20° C. The resulting solution was stirred at 20° C. for 2 hours and then allowed to settle before adding it to a suspension of sodium triacetoxyborohydride (25.8 Kg, 122 mol) in DCM (123 L) over 90 minutes maintaining the temperature below 30° C. The reaction mixture was stirred at 20° C. for 1 hour before quenching with an aqueous solution of potassium carbonate (36.4 Kg in 136 L of water) and the phases were allowed to separate. The organic phase was washed with water (2×23 L). The equipment was set for distillation and DCM (190 L) was removed by distillation to give a final volume of 45 litres. The mixture was cooled to 20° C. Yield 100% (51.1 Kg, 50.9% w/w in DCM). δH (CDCl3, 300 MHz) 0.8-1.0 (6H, m), 1.50-1.70 (2H, m), 2.10 (6H, s), 2.50-3.15 (5H, m), 3.50 (2H, dd), 4.80 (1H, dd), 5.90 (2H, s), 7.20 (1H, m), 7.80-7.90 (1H, m), 8.60 (1H, m) ppm. MS m/z 332 (MH+).

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